Pyridine → N-(5-fluoro-2-methylphenyl)methanesulfonamide

HRID 607515Notes

Reaction equation

HRID 607515 reaction equation
[N:1]1C=CC=CC=1.[F:7][C:8]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:9]=1N.[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl>[F:7][C:8]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([NH:1][S:17]([CH3:16])(=[O:19])=[O:18])[CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 2629702-Fluoro-5-methylaniline

Product 1

HCID 6466945N-(5-fluoro-2-methylphenyl)methanesulfonamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a pyridine (20 ml) and DCM (40 ml) solution of 2-fluoro-5-methylaniline (purchased from ACROS, 3.5 g, 28 mmol), methanesulfonyl chloride (purchased from WAKO, 4.3 ml, 56 mmol) was added at room temperature and the mixture was stirred for 20 hours. The reaction was quenched with 2M sodium hydroxide aqueous solution and the aqueous layer was separated and washed with DCM. The layer was cooled to 0° C. and acidified to pH 2.0 using 2M HCl aqueous solution. The precipitates were collected, and the solvent evaporated in vacuo, to give the title compound (5.1 g, 90%). MS (ESI) m/z 202 (M−H)−

Workup

  1. customThe reaction was quenched with 2M sodium hydroxide aqueous solution
  2. customthe aqueous layer was separated
  3. washwashed with DCM
  4. customThe precipitates were collected
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-bc7cc54f9141480f9fbfc243d73ea00f
Source dataset
uspto-grants-2011_03
Patent number
US07915448B2

Reaction notes

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